- Crosses the Line Twice: What does Gordon Freeman do upon finding out that his Dating Sim Loop is not what it seems to be? Shoot himself dead, simply because he doesn't want to deal with the rest of the Loop thanks to his prior experience with School Days (actually not a bad call given what DDLC devolves into). May overlap with Harsher in Hindsight given that the Awake Dokis reveal they're none too happy with him in Chapter 19...
- Hilarious in Hindsight:
- In Chapter 17.11, Monika and Natsuki bet that if "sexy Bowser" becomes a meme, they'll become bad Sonic OCs for a Loop. At the time, it was obviously not going to happen due to the obvious niches a sexy Bowser could be... and then Bowsette happened and the two had to follow through (Chapter 22.6).
- In Chapter 6.5, a text box reading "There can be happiness in the literature club! Unlock Monika's Route for only $9.99!" appears, angering Monika (who calls it "cruel and insulting", with Yuri agreeing that it seems "rather insensitive"). DDLC+ does have a route that can lead to happiness in the Literature Club... and is $14.99. Monika's not going to be happy when she finds out.
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